<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4803</id>
  <title>T3D4748</title>
  <common-name>Methyltestosterone</common-name>
  <description>A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.</description>
  <cas>58-18-4</cas>
  <pubchem-id>6010</pubchem-id>
  <chemical-formula>C20H30O2</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>163°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>33.9 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>The methyl group aids to increase oral bioavailability.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5&amp;alpha;-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5&amp;alpha;-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.</mechanism-of-toxicity>
  <metabolism>Hepatic.
Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).
Route of Elimination: 90% urine / 10% feces
Half Life: 6-8 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:14:39Z</created-at>
  <updated-at type="dateTime">2026-05-14T18:23:04Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Methyltestosterone</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07198</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>27436</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB06710</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</moldb-smiles>
  <moldb-formula>C20H30O2</moldb-formula>
  <moldb-inchi>InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1</moldb-inchi>
  <moldb-inchikey>GCKMFJBGXUYNAG-HLXURNFRSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">302.451</moldb-average-mass>
  <moldb-mono-mass type="decimal">302.224580204</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.36</logp>
  <hmdb-id>HMDB15655</hmdb-id>
  <chembl-id>CHEMBL1395</chembl-id>
  <chemspider-id>5788</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003705</chemdb-id>
  <dsstox-id>DTXSID1033664</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>(1S,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one</iupac>
  <moldb-polar-surface-area>37.3</moldb-polar-surface-area>
  <moldb-refractivity>89.068</moldb-refractivity>
  <moldb-polarizability>35.85049910033874</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>2</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>19.08673818044445</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-0.5280694266992777</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>3.61</moldb-alogps-logp>
  <moldb-alogps-logs>-4.34</moldb-alogps-logs>
  <moldb-alogps-solubility>1.39e-02 g/l</moldb-alogps-solubility>
</compound>
